By Joel Dresang

I need to cull more than 1,500 articles from our website before the current site’s content can be migrated to a new one. And the task has posed an existential challenge for me.

It’s like downsizing from a place where you’ve been accumulating stuff for 14 years and realizing you can’t take it all with you. But the website articles aren’t just boxes of old t-shirts I don’t wear anymore.

The articles represent me. I created them – picking the topics, researching the facts, organizing, composing, finding illustrations, adding links – all in line with Landaas & Company’s mission to educate individuals about investing. More than 90 of those articles are personal essays in which I divulged my own ignorance and enlightenment.

The struggle I face cutting content is a wake-up call to something bigger: How to define and pass along my legacy.

We often think of legacy in terms of wealth. Many of us have funded retirements through which we expect to live comfortably and still have some money left over for our children or charity. Retirement discussions with investment advisors need to include what to do with the remainder when we’re gone.

I’ve written about financial legacy more specifically in this article and this article and this article. And I suppose I view those articles as examples of my legacy.

To be clear, my existential dilemma isn’t so much about material I need to cut from the company website. That’s straightforward. My puzzle is more about the four boxes in our basement containing newspaper clips from 24 years as a reporter. Another box holds videotapes from my three years as a TV journalist and more as a freelancer. And then there’s a collection of spiral-bound notebooks I used as journals from eighth grade through 2003.

Why am I keeping all that work, if not as a legacy? I haven’t poked into those materials more than a dozen times over the years. Yet, part of me expects my wife and daughters to dig through them someday and – I don’t know, unfold mind-blowing discoveries about me.

“Creating and transmitting a legacy is one way a person concludes their life story and projects key elements of identity as expressed in this life story forward to future generations,” researchers explained in the Journal of Aging Studies 20 years ago. “It grounds their life within the context of a past and a future.”

More recently, the rabbi who wrote the book, “What Will They Say About You When You’re Gone?” told the news site Next Avenue: “Legacy is an automatic way for people to crystallize the core values they believe, the life they want to lead, the character traits they should aspire to.”

In other words, legacy is a way for us to try to connect who we are – based on what we have, what we’ve done, what we profess – to how we want to be remembered.

For most people, being remembered for wealth is a lower priority. A study by the group formerly known as Merrill Lynch found that 94% of adults said the best measure of a successful life is being loved; just 10% chose wealth as the yardstick. In the same poll, 69% said they wanted most to be remembered for the memories they shared, vs. 4% for their wealth.

Even in spreading our wealth, though, we have opportunities to impart our values. Those who engage their heirs in advance of their demise, for instance, can share wisdom along with wealth.

In a 2023 article about giving while living – passing along inheritance before passing on, Art Rothschild applauded the intergenerational passage of wealth “and the benefit of sharing the skills and values necessary to perpetuate it.”

Even just talking about wealth can enrich families, Dave Sandstrom explained in another Money Talk article. That’s one of the reasons Dave encourages investors to bring loved ones with them to meet their investment advisor.

Consideration of others is the key to any kind of legacy. In all that I have read about both getting your financial affairs in order and not burdening your survivors with your cluttered junk, I have learned that I need to invest time and thought into what I’m leaving – and to communicate my intentions with others.

So, here’s my game plan with all my notebooks and clips and videos:

  1. Go through them myself, taking notes along the way.
  2. Based on what I’ve gleaned, distill the themes the collective material suggests about who I am and how I want to be remembered.
  3. Set aside those items that best highlight the themes.
  4. Discard the rest (although maybe keep a limited number of pieces I particularly like that don’t fit the themes).
  5. Let my family know what I’m doing, in case any of them would like to join in.
  6. Write an overview explaining what I think the remaining works say about what I have valued.

My approach to this has been used in various ways by others to address how to handle the stuff they have amassed over a lifetime. The hard part is when you acknowledge that what might have seemed important to you might not be wanted by the people you’re bequeathing it to.

Advice I’ve read is that you shouldn’t take it personally. Just focus on conveying the story you’d hope others would tell about you when you’re no longer around. To do that, you first have to understand the story yourself.

Thinking this through has helped me realize that those files of yellowing newsprint aren’t keepsakes as much as they’re documents of experiences that have helped make me who I am. Sorting through them should allow me to put my work life in perspective and help me position myself for the next phase.

Joel Dresang is vice president-communications at Landaas & Company, LLC.

(initially posted March 28, 2024)